Confessions from Craigslist Casual Encounters

August 15, 2015
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Confessions from Craigslist Casual Encounters

Ah, Craigslist… that wonderful website you can use to find a place to live, household furniture, jobs, and a casual sex partner. A friend of mine we will call Julia allowed me to share her last casual encounter; no matter what you think, trolling for meaningless sex with a stranger requires a certain amount of courtesy and manners.

Julia’s story is a great example of the do’s and dont’s of appropriate no-strings-attached fucking. Julia was never the settling down type, so I knew she was serious about the man in her life when she said: “This is the one I’m going to marry.” At this point, Rob and Julia were discussing having a relationship; no decisions had been made, and they were still temporarily able to sleep with whomever they felt like. Rob was leaving on business and they put a pin on this discussion until he came back. About five days into his absence, Julia told me she’d had an incredibly sexual dream. One of those dreams that is so fucking hot, you wake up turned on. “Vanessa, I don’t remember the exact details of the dream, just that I was writhing in ecstasy, with this beautiful man that wasn’t Rob,” Julia said.

Once Julia woke up and realized it was a dream, it dawned on her that her footloose and fancy free days were going to be a thing of the past, very soon. “I just started to think, ‘oh my God, I can’t have random sex with strangers anymore’ and something came over me. I grabbed my laptop and I went somewhere I hadn’t been in three years… Craigslist Casual Encounters,” Julia said.

Craigslist Casual Encounters is a place you can visit online when you feel like getting fucked without all the bullshit hassle. There is nothing quite like fucking a stranger: someone who doesn’t know you, doesn’t care to know you, and won’t judge you, while you proceed to have some of the dirtiest, nastiest, most satisfying sex possible.

Julia began scanning the ads; the majority of them contained a dick pic and a few sentences. “I had forgotten how atrocious some of these ads are: ‘looking for cum slut,’ ‘let me jerk off on your face’, ‘daddy looking for college girl to spoil ad spank,’ ‘want to be my dirty little pain slut.’” Julia kept scrolling, until she found an ad entitled ‘NSA fun.’ In it was a nice paragraph about wanting to have hot sex, with an amazing dick pic attached. Let’s face facts, folks; most women are looking for a nice big cock, whether they admit it or not.

Julia responded to his ad, and included a pic of herself. Within a few minutes, she got a response from her casual encounter, whom we will call Dirk Diggler. Dirk sent her a face pic, which revealed a lovely handsome man. They began sexting and sending racier pics to one another. Julia told me: “The chemistry was hot even on the phone, so I knew, the sex would probably match. I told him I wanted to be bad and he said, ‘be bad with me,’ so we set a time. Maybe it was the ease of our texting, but I just knew this was going to be a really good fucking time.” Promptly at 7:30 p.m., Julia’s door bell rang and low and behold, there was Dirk, looking handsome like his photo.

Confessions from Craigslist Casual Encounters

She invited him in and the chemistry was immediately there. She poured them some wine while they sat on the couch. This part of the casual encounter is what I call ‘the dance’—in other words, how much small talk do I have to endure, until I’m riding your cock like the pony I never had. About three minutes into the chit-chat, Julia realized she was playing with a novice to this game. Dirk said to her: “Isn’t it amazing, we start a conversation on Craigslist and now we are here and we’re going to fuck… Funny how things work out.” Julia felt like he was saying that to reassure himself that they were indeed going to have sex. She found him amusing, like a cat finds a mouse amusing. The small talk continued and he undid his belt dramatically while talking, as if to once again reinforce that he wanted to pull his dick out.

Julia decided it was best just to take control of the situation, before she got annoyed. She got up to refill his glass and made sure her ass was right in front of his face as she bent over; he took the cue and put his hand up her skirt, caressing her thigh and grabbing her ass with the other hand. Julia turned around so she could straddle him on the couch. They began to furiously make out while she grinded on him like a well-trained stripper gives a lap dance. Julia led him into the bedroom (with many condoms visible next to the bed) and they were naked in seconds. Julia began to go down on his huge cock: “I wanted to see how much of it I could get in my mouth before I choked. You know my policy: if a dick is in my mouth, and I’m not crying a little bit, it shouldn’t be in there,” Julia said.

The condom went on and Dirk began sliding inside her. He was teasing her a bit putting the tip in and taking his time, before he was all the way in: “He’s teasing me with just the tip until I was begging for it, and then he was all the way inside me and Jesus fucking Christ, that thing was no joke. He pinned my arms down and pounded the shit out of me, just the way I like. I made sounds I hadn’t made in a long time. He folded me in half and fucked me so hard. I had to have him flip me over, because him on top of me got a bit painful. He flipped me over on all fours; I got on top of him while he pulled my hair and fucked me from every angle possible. He fucked me for three hours, with breaks in between. At one point he was pounding on me so hard my head board was slamming against the wall—and it’s antique wood, so I had to put my hand up and grab it, because I didn’t want it to break, but I also didn’t want him to stop. Once we finished, he rubbed my feet and we both breathed heavily. Here’s where it get’s interesting. We began to chat and he shared with me how he’s new to the scene, admitting this was his first casual encounter, that he actually went through with,” Julia said.

Confessions from Craigslist Casual Encounters

Julia indulged his conversation, because she remembered when she was new to the sex-positive community and began experimenting. Julia and I met at a play party a few years ago and she had been to a number of slutty events. After a few minutes, Julia had reached her max. It’s like last call at a bar; you don’t have to go home, but you can’t stay here. She politely ushered him out and he asked her if he could keep in touch. Everyone says that, but usually you don’t hear from them again. Two days later, she got a text from Dirk: “Hey, could you email me links to the sexy places you told me about.”

Julia sent him an email with an overwhelming amount of links, hoping that would be the last she heard of him. Two days later she got a late night text from him, saying he was horny. She didn’t text back.Then he responded to her email with the links.

This email was amazing, because it was so inappropriate. Upon reading it, one would assume they had been having a love affair for years. My favorite part (she allowed me and some of our friends to read it, so we could all laugh at Dirk’s expense): “Words escape me as I type because I know our offline conversations are just so much more powerful.” That’s when both Julia and I threw up in our mouths a little bit, while laughing hysterically. Julia decided not to be rude, and attempted to get rid of him politely. This was not the way to go; you give someone a finger and they take the whole hand. Lesson number one, ladies: Don’t respond to someone just to be polite. We are conditioned as women not to be rude and then we end up interacting with someone only because we don’t want to hurt their feelings.

He then began to text her and email her regarding his Tinder dates, asking her for advice, while he whined about not getting a kiss from this girl on the first date. Then he asked Julia how he could fuck more women that he met online. Julia had enough of Dirk at this point, so she sent him a goodbye email stating that she was looking for a one night stand, not a new needy friend who expected her to help him get laid. She is not Dear Abby, for Christ’s sake. Julia blocked him on her phone, and after that email, Dirk finally got the hint.

“I got on Craigslist that day to give myself a private bachelorette party. I knew this carnival ride was closing and I wanted to have one more strange passenger before I shut it down. I wasn’t looking for a connection; I was looking for cock. While the sex was great, he almost ruined it by being such a fucking baby about the whole thing,” Julia said.

Take this story as a lesson, folks: casual encounters are just that. Don’t contact the other party again, unless you absolutely know that’s okay. Don’t send them ridiculous emails which make it seem like you two are in love—and, here is a thought, don’t act pathetic or creepy. Thank you Julia for allowing me to share your casual encounter with all of my readers. It was a great story, so perhaps Dirk served his purpose after all.

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